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Encyclopedia > Psilocin
Psilocin
Systematic (IUPAC) name
4-Hydroxy-N,N-dimethyl-tryptamine
Identifiers
CAS number 520-53-6
ATC code  ?
PubChem  ?
Chemical data
Formula C12H16N2O 
Mol. mass 204.27 g/mol
SMILES search in eMolecules, PubChem
Physical data
Melt. point 173–176 °C (343–349 °F)
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Psilocin_chemical_structure. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... PubChem is a database of chemical molecules. ... This article or section does not cite any references or sources. ... General Name, symbol, number carbon, C, 6 Chemical series nonmetals Group, period, block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated Mr) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... The simplified molecular input line entry specification or SMILES is a specification for unambiguously describing the structure of chemical molecules using short ASCII strings. ... The melting point of a crystalline solid is the temperature at which it changes state from solid to liquid. ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...

Legal status

Prohibited (S9)(AU) Schedule III(CA) Class A(UK) Schedule I(US) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... Anthem Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Federal constitutional monarchy and parliamentary democracy  -  Queen Elizabeth II  -  Governor-General Michael Jeffery  -  Prime Minister John Howard Independence from the United Kingdom   -  Constitution 1 January 1901   -  Statute of... The Controlled Drugs and Substances Act is Canadas federal drug control statute. ... Motto (Latin for From Sea to Sea) Anthem O Canada Royal anthem: God Save the Queen Capital Ottawa Largest city Toronto Official languages English, French Government Parliamentary democracy and federal constitutional monarchy  -  Monarch Queen Elizabeth II  -  Governor General Michaëlle Jean  -  Prime Minister Stephen Harper Establishment  -  Act of Union February... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ... Motto: (Out Of Many, One) (traditional) In God We Trust (1956 to date) Anthem: The Star-Spangled Banner Capital Washington D.C. Largest city New York City None at federal level (English de facto) Government Federal constitutional republic  - President George Walker Bush (R)  - Vice President Dick Cheney (R) Independence from...

Routes  ?


Psilocin,(4-HO-DMT) sometimes called psilocine or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid. It is found in most psychedelic mushrooms together with its close congener psilocybin. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances.[1] In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Psychedelic drugs are psychoactive drugs whose primary action is to alter the thought processes of the brain. ... The general group of pharmacological agents commonly known as hallucinogens can be divided into three broad categories: psychedelics, dissociatives, and deliriants. ... Mushroom(s) are the fleshy, spore-bearing fruiting bodies of fungi typically produced above ground on soil or on their food sources. ... Chemical structure of ephedrine, a phenethylamine alkaloid An alkaloid is, strictly speaking, a naturally occurring amine produced by a plant,[1] but amines produced by animals and fungi are also called alkaloids. ... Psychedelic mushrooms is a general term for fungi that contain psychoactive substances. ... A congener (from Latin roots meaning born together or within the same race or kind) has several different meanings depending on the field in which it is used. ... Psilocybin (also known as psilocybine) is a psychedelic alkaloid of the tryptamine family, found in psilocybin mushrooms. ... Convention on Psychotropic Substances Opened for signature February 21, 1971 in Vienna Entered into force August 16, 1976 Conditions for entry into force 40 ratifications Parties 175 The Convention on Psychotropic Substances is a United Nations treaty designed to control psychoactive drugs such as amphetamines, barbiturates, and psychedelics. ...


Psilocin is almost identical to the chemical structure of the chemical of another known hallucinogen, bufotenin. The only difference is the position of the hydroxyl (OH-) group on the benzene ring - in psilocin, the hydroxyl group is at the 4-position in the indole ring, and in bufotenin, the hydroxyl group is at the 5-position on the indole ring. Bufotenin, also spelled bufotenine, is also known under the names 5-hydroxy-DMT (5-OH-DMT) or dimethyl-serotonin and is a tryptamine related to the neurotransmitter serotonin. ...

Contents

History

The Swiss chemist Albert Hofmann and the laboratory assistant Hans Tscherter from Sandoz isolated psilocin and its phosphate ester psilocybin from Psilocybe mushrooms in 1959 guided by self-administration. Dr. Dr. Albert Hofmann (born January 11, 1906) is a prominent Swiss scientist best known as the father of LSD. He was born in Baden, Switzerland, and studied chemistry at the University of Zürich. ... Sandoz Laboratories was a Swiss pharmaceutical company, best known for inventing LSD in 1938 and later marketing it as a psychiatric drug under the trade name Delysid. ... A carboxylic acid ester. ... This article or section is missing citation of sources. ...


Chemistry

Psilocin can be obtained by dephosphorylation of natural psilocybin under strongly acidic or under alkaline conditions (hydrolysis). One synthetic route uses the Speeter-Anthony tryptamine synthesis starting from 4-hydroxyindole. A phosphorylated serine residue Phosphorylation is the addition of a phosphate (PO4) group to a protein or a small molecule or the introduction of a phosphate group into an organic molecule. ... Acidity redirects here. ... Acids and bases: Acid-base reaction pH Self-ionization of water Buffer solutions Systematic naming Acid-base extraction Acidity function Proton affinity Acids: Strong acids Weak acids Superacids Lewis acids Mineral acids Organic acids Bases: Strong bases Weak bases Superbases Lewis bases Organic bases edit In chemistry, a base is... Hydrolysis is a chemical reaction or process in which a chemical compound reacts with water. ... In chemistry, chemical synthesis is purposeful execution of chemical reactions in order to get a product, or several products. ...


Psilocin is relatively unstable in solution due to its phenolic OH group. Under alkaline conditions in the presence of oxygen it immediately forms bluish and dark black degradation products. Similar products are also formed under acidic conditions in the presence of oxygen and Fe3+ ions (Keller's reagent, FeCl3 / MeOH / HCl). Psilocin is an amine and forms salts with acids [citation needed] that are usually more stable upon storage. Psilocin base can be evaporated by heating. In organic chemistry, phenols, sometimes called phenolics, are a class of chemical compounds consisting of a hydroxyl group (-OH) attached to an aromatic hydrocarbon group. ... This prefix in chemical nomenclature indicates the presence of a hydroxyl functional group (-OH). ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... General Name, symbol, number iron, Fe, 26 Chemical series transition metals Group, period, block 8, 4, d Appearance lustrous metallic with a grayish tinge Standard atomic weight 55. ... The general structure of an amine Amines are organic compounds and a type of functional group that contain nitrogen as the key atom. ... For other uses, see Salt (disambiguation). ... This article or section is in need of attention from an expert on the subject. ...


Pharmacology

Psilocybin is rapidly dephosphorylated in the body to psilocin which then acts as a partial agonist at the 5-HT2A serotonin receptor in the brain where it mimics the effects of serotonin (5-HT). Psilocin is an 5-HT1A and 5-HT2A/2C agonist.


See also

Psychedelic mushrooms is a general term for fungi that contain psychoactive substances. ... Psilocybin (also known as psilocybine) is a psychedelic alkaloid of the tryptamine family, found in psilocybin mushrooms. ... Tryptamine (3-(2-aminoethyl)indole) is a monoamine compound that is widespread in nature. ... Indole is an aromatic heterocyclic organic compound. ... Psychedelic drugs are psychoactive drugs whose primary action is to alter the thought processes of the brain. ... An assortment of psychoactive drugs A psychoactive drug or psychotropic substance is a chemical substance that acts primarily upon the central nervous system where it alters brain function, resulting in temporary changes in perception, mood, consciousness and behavior. ... For other uses, see Mana (disambiguation). ... Ayahuasca (Quechua, pronounced ) is any of various psychoactive infusions prepared from the Banisteriopsis spp. ... This article is about the Vedic plant and ritual. ...

References

  1. ^ "Green list"

External links

  • The Ones That Stain Blue Studies in ethnomycology including the contributions of Maria Sabina, Dr. Albert Hofmann and Dr. Gaston Guzman.
  • The Shroomery Detailed information about Psilocybin mushrooms including identification, cultivation and spores, psychedelic images, trip reports, a dosage calculator and an active community.
  • 4-HO-DMT entry in TiHKAL

  Results from FactBites:
 
Psilocin - Wikipedia, the free encyclopedia (261 words)
Psilocin, sometimes misspelled psilocine or psilotsin, is a psychedelic (hallucinogenic) mushroom alkaloid.
Psilocin is relatively unstable in solution due to its phenolic OH group.
Psilocin is the pharmacologically active agent in the body after ingestion of psilocybin or psychedelic mushrooms.
Psilocin - DFWIKI (127 words)
Psilocin ist ein Pilz-Alkaloid und ein Derivat der psychedelischen Substanz Psilocybin.
Psilocin entsteht durch Dephosphorylierung von Psilocybin unter stark sauren oder alkalischen Bedingungen.
Psilocin ist das pharmakologisch aktive Prinzip nach Einnahme von Psilocybin oder halluzinogenen Pilzen.
  More results at FactBites »

 
 

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